What makes a great interview? This podcaster sat down with interviewing legends to find out

That soundbite kicks off the preview for Jesse Thorn's new podcast, The Turnaround. So, what is an interview?

"I think that interviewing is so many different things," said Thorn, the founder of MaximumFun.org, an independent podcast and radio production organization. "Everything I know about interviewing is something that I made up for myself in my own head."

Trying to understand what makes a good interviewer a great one: that's what Thorn's trying to figure out with The Turnaround. Among the industry giants Thorn sat down with include Katie Couric, Ira Glass, Terry Gross, Larry King and Jerry Springer. Yep, you read that last one right.

A partnership between Columbia Journalism Review and MaximumFun, the show will premiere June 22 and run twice a week all summer. Thorn, who has hosted the culture podcast Bullseye since he was in college more than 17 years ago, the entire experience has been an education.

"I never worked for anyone as a journalist," he said. "I never had a journalism mentor. I never had an interviewing mentor. (This podcast) was a little bit like a weird form of journalism school for me."

Poynter caught up with Thorn to talk about the upcoming release of The Turnaround, how all journalists can become better interviewers and how age and upbringing influence a podcasters' style. This Q-and-A has been shortened for clarity.

First things first: What have you learned so far about interviewing?

For me, the part of interviewing that I struggle with the most is engaging with a...sort of genuine, deep spontaneity. So, while I think you could make an argument — and certainly many have — that Larry King is not a great interviewer but rather a bad interviewer, and I think he’s mostly a great interviewer.

I think I maybe learned the most from Larry King. Because Larry King is the person that I spoke to who was most deeply connected to their own curiosity. And that is something that I think a lot of people are scared to do because asking a question you genuinely don’t know the answer to can lead to you looking dumb.

I went to his house to do the interview, which was unusual, but he’s Larry King. He was kind enough to share his time, and we sat in his room full of memorabilia, which was unbelievable. (Laughs) But he sits down, he doesn’t know me from Adam, asks me a couple questions about myself and he is immediately, completely, entirely there with me. And seeking to generate that feeling is something I learned about significantly from him, and sort of pushed forward in my mind and my heart when I’m doing my own work because of that conversation with him.

So, you sat down with Larry King, and you’re striving for this more personal connection. Through that interview and others you’ve done for the podcast, do you feel like your own interviewing techniques have gotten better?

Certainly, that was my goal. I never went to journalism school. The closest that I ever came was I worked as an intern for a great public radio show out of the Bay Area called West Coast Live, and the host of that show, Sedge Thomson, is a very brilliant interviewer. I learned something from hanging around there, but there was never a Q-and-A. And part of my goal was almost to just compare notes with people and just say, ‘Hey, does this seem right?’ Because I made it up in my own head and never had anyone to correct me.

Asking people with all these different backgrounds, from one of my public radio heroes Ray Suarez, to Jerry Springer, who walks into every episode of his show genuinely not knowing what’s going on with the people who are on stage — intentionally. So, if I didn’t get better, than I probably did a bad job on the show (Laughs).

You mentioned that you interviewed Jerry Springer for the show. Why?

There’s no doubt that the reason Jerry Springer is successful is because he’s good at his job. I mean, we 100 percent wanted to have someone from daytime television on the show, because daytime television is where most of the most-watched talk programming in America is. So...Jerry Springer is the iconic face of that. I know we tried to get Wendy Williams, and we tried to get Oprah, (we) got polite no’s from their people.

But you know, Jerry Springer is a guy who is capable of managing madness. That is his gift, and that is the thing that has made him so good at hosting his show, is that when he walks on stage with an index card and asks somebody, ‘So, why are you here today?’ and they say, ‘Oh, I’m here because I’m in love with my horse.’ And then he goes from there and fills 18 minutes of television with that. And that’s an incredible skill.

Does the show ever just feel really meta to you?

Oh, the whole thing is profoundly meta! I mean, one of the things about this show was that it was important to me that we have no plan to make money from this show, because that felt like cheating to me (Laughs). Like, I spent a lot of money making this show because I paid my producers while they were producing the show, but I didn’t want to have any income from the show in part because I didn’t want anyone to call me out on the fact that it was absurd to do an interviewing show about interviewing that was obviously just an interviewing class for me, the interviewer.

So yeah, it’s definitely ‘Through the Looking Glass.’ I’ve been doing an interview show every week since I was 19 years old, and I’m 36, so 17 years. My instinct is to include the audience and to make no presumptions about the audience. So, while this show is sillier and maybe somewhat more digressive and lower stakes than what I do on NPR, I am still working to make sure that it would mean something to a person who just happened to click on it in Apple Podcasts, as well as mean something to somebody who has the same job as me, or is like me at age 20 at that college radio station reviewing albums to get enough volunteer hours to get a show.

You also host Bullseye, and I feel like transitioning from that podcast to this one would be interesting. How have you dealt with going from interviewing people like Big Boi of Outkast to people like Katie Couric?

Well, I think early on I committed myself to not expending too much emotional energy on The Turnaround. Because my expenditures of emotional energy tend to be in the form of nerves, fear, discomfort, over-preparation, guilt — negative things. I never am excited about an interview, at least until I get in the booth or sometimes when it’s over. So I said to myself, ‘Look, this is a cool project that you’re doing to learn things, you like these people, they are substantially your peers in some way … so just enjoy talking to them and see what you can learn.’ And I think the only time I failed that was with Terry Gross.

I had never met Terry Gross in my life, and I host a show that is a knockoff of Terry Gross’ show. I mean, there are things that are different about my show and her show; I have a very different perspective from what her show has and I have a different style than she has. But, you know, eventually I’m doing an alternative version of her show. And I was very intimidated to talk to her. I also was very sick.

And so here I was, talking down a microphone through a phone line to Philadelphia, where my hero is sitting behind microphone talking to me and sharing time with me, and I am barely coherent, and exhausted, and sick and confused. I was basically in the state that a boxer is after he just lost a 12-round decision. And she couldn’t have been more lovely. I haven’t listened to the tape because I’m scared that I did a really bad job.

But besides that, it was a matter of, ‘Hey, just go into the booth and talk to the person and see what you can learn.’ That was another advantage of the (fact that) I’m not going to make any money out of this. I presumed going in that this show would be a marketplace failure. There is a very narrow band of people who want to hear me interviewing interviewers about interviewing, so I figured I should probably not worry about it too much, and that worked pretty good. Whereas with any given Bullseye (episode), I’m worried about every single part of it. I’m sure that every part of it will bring me shame (Laughs).

And you’ve been working on Bullseye for 17 years, since you were in college, right?

Yeah, my entire adult life. The show used to be called The Sound of Young America, but other than that it’s been a continuously weekly production since I was 19.

I originally went down to the radio station thinking that making radio would probably be really hard. ...I got there and saw a mixing board and saw them using it and I was like, ‘Oh, so basically up is louder. I can handle that.’ And I signed up to volunteer and put in an offer for a show at the end of my freshman year of college.

You started when you were super young. You were actually one of the youngest podcast hosts that NPR has had, I believe.

When The Sound of Young America went national, which was when I was 26, I think I was the youngest national public radio host with NPR, PRI or anyone else — ever. It’s 10 years later, and I’m still either the youngest, or maybe Kelly McEvers is about my age. There’s a couple people now who are about my age, but we are the youngest still. (Laughs) And I’ve been national for 10 years and doing it for 17.

How do you think being one of the youngest in the field has influenced your style?

It’s a funny thing, you know. I think there is a generation now who has grown up on This American Life and always felt like there was room for a conversational tone, even if it was, in the case of This American Life, this kind of performative, abstracted version of a conversational tone.

And that is the expectation for what public radio can be. I think when I started This American Life was on the air, it was already inspiring people, but it wasn’t a lane that you were allowed in. And so for me, I think I had this idea of these things that I wanted a public radio show to be that there weren’t really out there, and I was trying to do that.

...Almost everyone in public radio comes from a news context, and particularly a hard news context. And so they pursue most of their output through a hard news style lens, and I did not even think of myself as a journalist until I signed with NPR a few years ago and they explained to me that I had to be a journalist and abide by their journalistic ethics code. I really thought of myself like, I don’t know, David Letterman or whatever.

So your show and your style are very different from mainstream podcasts. You mentioned This American Life, but I’m interested in how you envision The Turnaround being different from other journalism or self-help podcasts, such as Longform. How is your show different from that kind of show, and how is it similar?

I have not listened to Longform. The main podcast I listen to that is not produced by MaximumFun.org is called Effectively Wild. It’s about baseball, I listen to it because it never upsets me. I’m profoundly emotionally fragile; I just need something to listen to on my commute where the weightiest topic will be, ‘Will Billy Hamilton ever learn to hit?’ or ‘Why are there more position players pitching now?’

I mean, I think that interviewing is such an oddly specific task. ...And there’s no resources about how to do it, and there’s a shit ton about storytelling or whatever. And there’s a medium shit ton about reporting, like fact-gathering. But this is a show that is particularly about what it’s like to sit across from another person and talk to them. And there are reporters on it, but it is, I think, unique in that it is about that interchange specifically. And I know from having been the subject of journalism over the years that news and feature people’s skills in this area vary extraordinarily wildly. And this is a show about how to actually engage with somebody and actually learn something from them.

If you had to pick one interviewing technique that you’ve learned that all journalists should be using, but aren’t, what would that be?

There is a question that you can ask that I learned from This American Life’s comic book, which came out many years ago. And in it, Ira refers to one of those old public radio dudes who’s perfect at their job and has been doing it forever, that there is one question that you can ask in any situation. I am embarrassed to say this, but I probably use it every two weeks on average, so that would be one in three interviews, let’s say. And it is, essentially, ‘What did you think it was going to be like, what did it turn out to be, and how do they compare?’ And you can ask that about anything.

Ira explains that very insightfully. I mean, Ira is the first episode of The Turnaround because he is the person I know who has thought the most about his craft and why he makes every move that he makes. He’s a guy who worked at NPR for 20 years before he started This American Life, and I think that whole time he was plotting This American Life.

Ira is a genius with this. Ira says, ‘That is a perfect question because it automatically inspires reflection.' It inspires a compare and contrast that fundamentally asks, ‘What does this mean?’ And that is the work of most interviews, is to try and hear the story that contains the information and then hear the meaning of that. And people don’t usually offer both of those at the same time, but this question sort of automatically demands them.

I have to ask. What did you think your podcast would be like, how did it turn out and how do those two things compare?

I think that I imagined I would have more tips and tricks. I am terrible at getting people to give tips and tricks because I always just am enjoying talking to them, and then I forget to ask for gears and working parts. But, you know, I think one of the biggest things that I learned is that there is not a right way to do my job, and so I should stop worrying that I am doing it wrong. And instead, I should be thinking about a kind of broader philosophical question, which is: Am I open-hearted enough?

I know that sounds corny. But I really mean the challenge that I recognize for myself — that I did not anticipate recognizing — is the challenge to be really curious about the things that I’m really curious about, give myself permission to ask questions that I don’t know the answer to and to really care about finding out about other people. (Laughs)